Cutless bearings are hard to get out, one way is to take the blade off of a hack saw and reattach it with the blade thru the bearing (this is how the yard took one out for me) two cuts and you are out. There is also a tool to pull them with, good luck.
I have a PSS shaft seal. There is no drip or water entry at all when the boat is sitting or motoring flat. There is a little water that comes in when you are heeled over quite a bit, both motoring and sailing. I have been very happy with it.
